CA2144530C - Compositions a base de polyurethane assurant l'etancheite - Google Patents
Compositions a base de polyurethane assurant l'etancheite Download PDFInfo
- Publication number
- CA2144530C CA2144530C CA002144530A CA2144530A CA2144530C CA 2144530 C CA2144530 C CA 2144530C CA 002144530 A CA002144530 A CA 002144530A CA 2144530 A CA2144530 A CA 2144530A CA 2144530 C CA2144530 C CA 2144530C
- Authority
- CA
- Canada
- Prior art keywords
- percent
- isocyanate
- prepolymer
- silane
- sealant
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 46
- 239000004588 polyurethane sealant Substances 0.000 title claims abstract description 12
- 229920001228 polyisocyanate Chemical group 0.000 claims abstract description 40
- 239000005056 polyisocyanate Chemical group 0.000 claims abstract description 39
- 239000000565 sealant Substances 0.000 claims abstract description 34
- -1 amino-alkoxy silane Chemical group 0.000 claims abstract description 21
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical group [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims abstract description 20
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims abstract description 18
- 239000011521 glass Substances 0.000 claims abstract description 17
- 229910000077 silane Inorganic materials 0.000 claims abstract description 16
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims abstract description 14
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 12
- 239000000758 substrate Substances 0.000 claims abstract description 12
- 229910052751 metal Inorganic materials 0.000 claims abstract description 5
- 239000002184 metal Substances 0.000 claims abstract description 5
- 150000001875 compounds Chemical class 0.000 claims description 17
- 125000001931 aliphatic group Chemical group 0.000 claims description 9
- 239000012948 isocyanate Substances 0.000 claims description 9
- 150000002513 isocyanates Chemical class 0.000 claims description 9
- 150000001412 amines Chemical class 0.000 claims description 7
- 239000005057 Hexamethylene diisocyanate Substances 0.000 claims description 6
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- 125000000962 organic group Chemical group 0.000 claims description 2
- 229920005862 polyol Polymers 0.000 description 17
- 150000003077 polyols Chemical class 0.000 description 17
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- BUZRAOJSFRKWPD-UHFFFAOYSA-N isocyanatosilane Chemical compound [SiH3]N=C=O BUZRAOJSFRKWPD-UHFFFAOYSA-N 0.000 description 10
- 230000001070 adhesive effect Effects 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- 239000000853 adhesive Substances 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 6
- 229920000642 polymer Polymers 0.000 description 6
- ZMSQJSMSLXVTKN-UHFFFAOYSA-N 4-[2-(2-morpholin-4-ylethoxy)ethyl]morpholine Chemical compound C1COCCN1CCOCCN1CCOCC1 ZMSQJSMSLXVTKN-UHFFFAOYSA-N 0.000 description 5
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 229920005989 resin Polymers 0.000 description 5
- 239000011347 resin Substances 0.000 description 5
- 239000005058 Isophorone diisocyanate Substances 0.000 description 4
- 239000004721 Polyphenylene oxide Substances 0.000 description 4
- 239000011324 bead Substances 0.000 description 4
- 239000006229 carbon black Substances 0.000 description 4
- 239000004927 clay Substances 0.000 description 4
- 239000006185 dispersion Substances 0.000 description 4
- 125000001261 isocyanato group Chemical group *N=C=O 0.000 description 4
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 4
- 239000004014 plasticizer Substances 0.000 description 4
- 229920000570 polyether Polymers 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical class C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical class CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 239000003999 initiator Substances 0.000 description 3
- 150000005846 sugar alcohols Polymers 0.000 description 3
- KSBAEPSJVUENNK-UHFFFAOYSA-L tin(ii) 2-ethylhexanoate Chemical compound [Sn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O KSBAEPSJVUENNK-UHFFFAOYSA-L 0.000 description 3
- QKOWXXDOHMJOMQ-UHFFFAOYSA-N 1,3,5-tris(6-isocyanatohexyl)biuret Chemical compound O=C=NCCCCCCNC(=O)N(CCCCCCN=C=O)C(=O)NCCCCCCN=C=O QKOWXXDOHMJOMQ-UHFFFAOYSA-N 0.000 description 2
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 2
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical class [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 description 2
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 2
- 125000005442 diisocyanate group Chemical group 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 239000005357 flat glass Substances 0.000 description 2
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 2
- 235000011187 glycerol Nutrition 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 2
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 229920005906 polyester polyol Polymers 0.000 description 2
- 229920001451 polypropylene glycol Polymers 0.000 description 2
- 230000002028 premature Effects 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- 150000003335 secondary amines Chemical group 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000000600 sorbitol Substances 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 description 2
- 239000003981 vehicle Substances 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- NIDNOXCRFUCAKQ-UMRXKNAASA-N (1s,2r,3s,4r)-bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid Chemical compound C1[C@H]2C=C[C@@H]1[C@H](C(=O)O)[C@@H]2C(O)=O NIDNOXCRFUCAKQ-UMRXKNAASA-N 0.000 description 1
- KMOUUZVZFBCRAM-UHFFFAOYSA-N 1,2,3,6-tetrahydrophthalic anhydride Chemical compound C1C=CCC2C(=O)OC(=O)C21 KMOUUZVZFBCRAM-UHFFFAOYSA-N 0.000 description 1
- ZTNJGMFHJYGMDR-UHFFFAOYSA-N 1,2-diisocyanatoethane Chemical compound O=C=NCCN=C=O ZTNJGMFHJYGMDR-UHFFFAOYSA-N 0.000 description 1
- LTMRRSWNXVJMBA-UHFFFAOYSA-L 2,2-diethylpropanedioate Chemical compound CCC(CC)(C([O-])=O)C([O-])=O LTMRRSWNXVJMBA-UHFFFAOYSA-L 0.000 description 1
- YEVQZPWSVWZAOB-UHFFFAOYSA-N 2-(bromomethyl)-1-iodo-4-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=C(I)C(CBr)=C1 YEVQZPWSVWZAOB-UHFFFAOYSA-N 0.000 description 1
- KRQUFUKTQHISJB-YYADALCUSA-N 2-[(E)-N-[2-(4-chlorophenoxy)propoxy]-C-propylcarbonimidoyl]-3-hydroxy-5-(thian-3-yl)cyclohex-2-en-1-one Chemical compound CCC\C(=N/OCC(C)OC1=CC=C(Cl)C=C1)C1=C(O)CC(CC1=O)C1CCCSC1 KRQUFUKTQHISJB-YYADALCUSA-N 0.000 description 1
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical class C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 1
- AZFJDAIILPPZJN-UHFFFAOYSA-N 4-[2-[2-(3,5-dimethylmorpholin-4-yl)ethoxy]ethyl]-3,5-dimethylmorpholine Chemical compound CC1COCC(C)N1CCOCCN1C(C)COCC1C AZFJDAIILPPZJN-UHFFFAOYSA-N 0.000 description 1
- 229930185605 Bisphenol Natural products 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 241000590810 Corades Species 0.000 description 1
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
- MQIUGAXCHLFZKX-UHFFFAOYSA-N Di-n-octyl phthalate Natural products CCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCC MQIUGAXCHLFZKX-UHFFFAOYSA-N 0.000 description 1
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- 229930195725 Mannitol Natural products 0.000 description 1
- 229920001730 Moisture cure polyurethane Polymers 0.000 description 1
- IIGAAOXXRKTFAM-UHFFFAOYSA-N N=C=O.N=C=O.CC1=C(C)C(C)=C(C)C(C)=C1C Chemical compound N=C=O.N=C=O.CC1=C(C)C(C)=C(C)C(C)=C1C IIGAAOXXRKTFAM-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 229920000538 Poly[(phenyl isocyanate)-co-formaldehyde] Polymers 0.000 description 1
- 229920002396 Polyurea Polymers 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- AWMVMTVKBNGEAK-UHFFFAOYSA-N Styrene oxide Chemical compound C1OC1C1=CC=CC=C1 AWMVMTVKBNGEAK-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- UWHCKJMYHZGTIT-UHFFFAOYSA-N Tetraethylene glycol, Natural products OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical class C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 1
- 229910021626 Tin(II) chloride Inorganic materials 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- YKTSYUJCYHOUJP-UHFFFAOYSA-N [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] Chemical compound [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] YKTSYUJCYHOUJP-UHFFFAOYSA-N 0.000 description 1
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 1
- 239000011358 absorbing material Substances 0.000 description 1
- 150000001241 acetals Chemical class 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 150000001279 adipic acids Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- BJQHLKABXJIVAM-UHFFFAOYSA-N bis(2-ethylhexyl) phthalate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1C(=O)OCC(CC)CCCC BJQHLKABXJIVAM-UHFFFAOYSA-N 0.000 description 1
- OHJMTUPIZMNBFR-UHFFFAOYSA-N biuret Chemical group NC(=O)NC(N)=O OHJMTUPIZMNBFR-UHFFFAOYSA-N 0.000 description 1
- 238000012662 bulk polymerization Methods 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 description 1
- VKONPUDBRVKQLM-UHFFFAOYSA-N cyclohexane-1,4-diol Chemical compound OC1CCC(O)CC1 VKONPUDBRVKQLM-UHFFFAOYSA-N 0.000 description 1
- 238000007872 degassing Methods 0.000 description 1
- PNOXNTGLSKTMQO-UHFFFAOYSA-L diacetyloxytin Chemical compound CC(=O)O[Sn]OC(C)=O PNOXNTGLSKTMQO-UHFFFAOYSA-L 0.000 description 1
- 239000012975 dibutyltin dilaurate Substances 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- POULHZVOKOAJMA-UHFFFAOYSA-M dodecanoate Chemical compound CCCCCCCCCCCC([O-])=O POULHZVOKOAJMA-UHFFFAOYSA-M 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- GKIPXFAANLTWBM-UHFFFAOYSA-N epibromohydrin Chemical compound BrCC1CO1 GKIPXFAANLTWBM-UHFFFAOYSA-N 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- VANNPISTIUFMLH-UHFFFAOYSA-N glutaric anhydride Chemical compound O=C1CCCC(=O)O1 VANNPISTIUFMLH-UHFFFAOYSA-N 0.000 description 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
- 229930182470 glycoside Natural products 0.000 description 1
- 150000005826 halohydrocarbons Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- MUTGBJKUEZFXGO-UHFFFAOYSA-N hexahydrophthalic anhydride Chemical compound C1CCCC2C(=O)OC(=O)C21 MUTGBJKUEZFXGO-UHFFFAOYSA-N 0.000 description 1
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- TZMQHOJDDMFGQX-UHFFFAOYSA-N hexane-1,1,1-triol Chemical compound CCCCCC(O)(O)O TZMQHOJDDMFGQX-UHFFFAOYSA-N 0.000 description 1
- ACCCMOQWYVYDOT-UHFFFAOYSA-N hexane-1,1-diol Chemical compound CCCCCC(O)O ACCCMOQWYVYDOT-UHFFFAOYSA-N 0.000 description 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 1
- 125000001841 imino group Chemical group [H]N=* 0.000 description 1
- 238000009434 installation Methods 0.000 description 1
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical group OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 1
- 229940070765 laurate Drugs 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- 229940117969 neopentyl glycol Drugs 0.000 description 1
- 229920003986 novolac Polymers 0.000 description 1
- OEIJHBUUFURJLI-UHFFFAOYSA-N octane-1,8-diol Chemical compound OCCCCCCCCO OEIJHBUUFURJLI-UHFFFAOYSA-N 0.000 description 1
- 229940049964 oleate Drugs 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 238000007539 photo-oxidation reaction Methods 0.000 description 1
- 239000008029 phthalate plasticizer Substances 0.000 description 1
- LGRFSURHDFAFJT-UHFFFAOYSA-N phthalic anhydride Chemical compound C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920001225 polyester resin Polymers 0.000 description 1
- 239000004645 polyester resin Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920006295 polythiol Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- ULWHHBHJGPPBCO-UHFFFAOYSA-N propane-1,1-diol Chemical class CCC(O)O ULWHHBHJGPPBCO-UHFFFAOYSA-N 0.000 description 1
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 description 1
- 229940080818 propionamide Drugs 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
- 150000004756 silanes Chemical class 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- AUHHYELHRWCWEZ-UHFFFAOYSA-N tetrachlorophthalic anhydride Chemical compound ClC1=C(Cl)C(Cl)=C2C(=O)OC(=O)C2=C1Cl AUHHYELHRWCWEZ-UHFFFAOYSA-N 0.000 description 1
- 239000012974 tin catalyst Substances 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 239000000326 ultraviolet stabilizing agent Substances 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 239000004591 urethane sealant Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/48—Polyethers
- C08G18/4804—Two or more polyethers of different physical or chemical nature
- C08G18/4812—Mixtures of polyetherdiols with polyetherpolyols having at least three hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/08—Processes
- C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/08—Processes
- C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
- C08G18/12—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step using two or more compounds having active hydrogen in the first polymerisation step
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/61—Polysiloxanes
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K3/00—Materials not provided for elsewhere
- C09K3/10—Materials in mouldable or extrudable form for sealing or packing joints or covers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2190/00—Compositions for sealing or packing joints
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Polyurethanes Or Polyureas (AREA)
- Sealing Material Composition (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US96009892A | 1992-10-13 | 1992-10-13 | |
| US07/960,098 | 1992-10-13 | ||
| PCT/US1993/008485 WO1994009046A1 (fr) | 1992-10-13 | 1993-09-09 | Compositions de materiau d'etancheite a base de polyurethanne |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2144530A1 CA2144530A1 (fr) | 1994-04-28 |
| CA2144530C true CA2144530C (fr) | 2005-07-26 |
Family
ID=25502793
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002144530A Expired - Lifetime CA2144530C (fr) | 1992-10-13 | 1993-09-09 | Compositions a base de polyurethane assurant l'etancheite |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US5623044A (fr) |
| JP (1) | JP3466610B2 (fr) |
| KR (1) | KR100285097B1 (fr) |
| CN (1) | CN1054148C (fr) |
| AU (1) | AU675083B2 (fr) |
| BR (1) | BR9307293A (fr) |
| CA (1) | CA2144530C (fr) |
| TW (1) | TW268045B (fr) |
| WO (1) | WO1994009046A1 (fr) |
| ZA (1) | ZA937549B (fr) |
Families Citing this family (117)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE69623817T2 (de) * | 1996-01-11 | 2003-07-31 | Essex Specialty Products, Inc. | Härtbare einkomponentenpolyurethanklebstoffe |
| AR005429A1 (es) * | 1996-01-11 | 1999-06-23 | Essex Specialty Prod | Prepolimeros de poliuretano, composiciones adhesivas en un solo envase que incluyen dichos prepolimeros y procedimiento para adherir substratos con dichascomposiciones |
| US5922809A (en) * | 1996-01-11 | 1999-07-13 | The Dow Chemical Company | One-part moisture curable polyurethane adhesive |
| CA2214311A1 (fr) * | 1996-09-06 | 1998-03-06 | Air Products And Chemicals, Inc. | Adhesifs thermofusibles contenant des prepolymeres d'isocyanate pauvres en monomeres libres, pauvres en oligomeres |
| US5852137A (en) * | 1997-01-29 | 1998-12-22 | Essex Specialty Products | Polyurethane sealant compositions |
| JP3263034B2 (ja) * | 1997-11-12 | 2002-03-04 | 横浜ゴム株式会社 | ポリウレタン組成物 |
| US6053971A (en) * | 1997-12-18 | 2000-04-25 | Essex Specialty Products, Inc. | Method to achieve improved adhesion of urethane adhesive to a painted surface |
| US5990257A (en) * | 1998-01-22 | 1999-11-23 | Witco Corporation | Process for producing prepolymers which cure to improved sealants, and products formed thereby |
| US6008305A (en) * | 1998-06-30 | 1999-12-28 | Adco Products, Inc. | Primer for improving the bonding of adhesives to nonporous substrates |
| US6096823A (en) * | 1998-10-14 | 2000-08-01 | Bayer Corporation | Moisture-curable compounds containing isocyanate and alkoxysilane groups |
| KR100631311B1 (ko) | 1999-02-05 | 2006-10-09 | 에섹스 스페시얼티 프로덕츠, 인코오포레이티드 | 폴리우레탄 실란트 조성물 |
| US6350799B1 (en) * | 2000-05-23 | 2002-02-26 | Lord Corporation | Coolant resistant and thermally stable primer composition |
| US7022206B2 (en) * | 2000-05-23 | 2006-04-04 | Lord Corporation | Coolant resistant and thermally stable primer composition |
| US6362300B1 (en) | 2000-07-06 | 2002-03-26 | The Yokohama Rubber Co., Ltd. | Moisture-curable polyurethane compositions |
| AU2001283149A1 (en) | 2000-08-07 | 2002-02-18 | Dow Global Technologies Inc. | One-part moisture curable polyurethane adhesive |
| JP4617547B2 (ja) * | 2000-08-08 | 2011-01-26 | 横浜ゴム株式会社 | プライマー組成物 |
| DE10132938A1 (de) * | 2001-07-06 | 2003-01-16 | Degussa | Nichtwässriges, wärmehärtendes Zweikomponenten-Beschichtungsmittel |
| WO2003048067A1 (fr) * | 2001-11-29 | 2003-06-12 | Dow Global Technologies Inc. | Procede de collage d'une fenetre sur un substrat sans emploi d'appret |
| DE10162642A1 (de) * | 2001-12-20 | 2003-07-10 | Henkel Kgaa | Haftvermittler für reaktive Polyurethane |
| KR20030057384A (ko) * | 2001-12-27 | 2003-07-04 | 요코하마 고무 가부시키가이샤 | 폴리우레탄 조성물 |
| US6649016B2 (en) | 2002-03-04 | 2003-11-18 | Dow Global Technologies Inc. | Silane functional adhesive composition and method of bonding a window to a substrate without a primer |
| US6878231B2 (en) * | 2003-02-28 | 2005-04-12 | Lord Corporation | One-part solvent-based adhesive for bonding polymer materials |
| JP2005139319A (ja) * | 2003-11-07 | 2005-06-02 | Yokohama Rubber Co Ltd:The | 硬化性樹脂組成物 |
| BRPI0417232A (pt) * | 2003-12-10 | 2007-03-06 | Dow Global Technologies Inc | composição para ligar vidro ou plástico, sistema adesivo para colar vidro em um substrato, método para ligar vidro ou plástico, automóvel, e método para ligar uma janela em um veìculo |
| CN100349902C (zh) * | 2003-12-22 | 2007-11-21 | 张家港市国泰华荣化工新材料有限公司 | 含异氰酸酯基团的硅烷的制备方法 |
| US7494540B2 (en) | 2004-12-15 | 2009-02-24 | Dow Global Technologies, Inc. | System for bonding glass into a structure |
| CN101228246B (zh) * | 2005-05-31 | 2011-12-07 | 陶氏环球技术有限责任公司 | 对油漆和玻璃制品无底漆的聚氨酯密封胶组合物 |
| US7781493B2 (en) | 2005-06-20 | 2010-08-24 | Dow Global Technologies Inc. | Protective coating for window glass |
| US7786183B2 (en) * | 2005-06-20 | 2010-08-31 | Dow Global Technologies Inc. | Coated glass articles |
| EP1760100A1 (fr) | 2005-09-01 | 2007-03-07 | Sika Technology AG | Produits d'addition contenant des groupes d'isocyanate et composés ayant une forte adhésion sur des substrats revêtus |
| DE102005045150A1 (de) | 2005-09-22 | 2007-04-05 | Basf Coatings Ag | Verwendung von Phosphonsäurediestern und Diphosphonsäurediestern sowie thermisch härtbare Gemische, enthaltend Phosphonsäurediester und Diphosphonsäurediester |
| US7345130B2 (en) * | 2005-10-25 | 2008-03-18 | Dow Global Technologies Inc. | Silane functional prepolymer and isocyanate functional prepolymer blend based adhesive composition |
| KR20080078860A (ko) * | 2005-12-30 | 2008-08-28 | 쓰리엠 이노베이티브 프로퍼티즈 컴파니 | 기능화 기판 |
| US20070175621A1 (en) * | 2006-01-31 | 2007-08-02 | Cooligy, Inc. | Re-workable metallic TIM for efficient heat exchange |
| US8580361B2 (en) * | 2006-02-01 | 2013-11-12 | Momentive Performance Materials Inc. | Insulated glass unit with sealant composition having reduced permeability to gas |
| US20070179236A1 (en) * | 2006-02-01 | 2007-08-02 | Landon Shayne J | Sealant composition having reduced permeability to gas |
| US20070178256A1 (en) * | 2006-02-01 | 2007-08-02 | Landon Shayne J | Insulated glass unit with sealant composition having reduced permeability to gas |
| US7569653B2 (en) | 2006-02-01 | 2009-08-04 | Momentive Performance Materials Inc. | Sealant composition having reduced permeability to gas |
| US7541076B2 (en) * | 2006-02-01 | 2009-06-02 | Momentive Performance Materials Inc. | Insulated glass unit with sealant composition having reduced permeability to gas |
| WO2007136710A2 (fr) * | 2006-05-18 | 2007-11-29 | Universal Biochemical, Inc. | Procédé d'augmentation de la vitesse de durcissement de systèmes à base de polyuréthane |
| DE102006024823A1 (de) * | 2006-05-29 | 2007-12-06 | Basf Coatings Ag | Verwendung von härtbaren Gemischen, enthaltend silangruppenhaltige Verbindungen sowie Phosphonsäurediester oder Diphosphonsäurediester, als Haftvermittler |
| US7955696B2 (en) * | 2006-12-19 | 2011-06-07 | Dow Global Technologies Llc | Composites and methods for conductive transparent substrates |
| RU2455329C2 (ru) * | 2006-12-19 | 2012-07-10 | ДАУ ГЛОБАЛ ТЕКНОЛОДЖИЗ ЭлЭлСи | Добавки, способствующие адгезии, и способы улучшения композиций для покрытия |
| WO2008077042A1 (fr) * | 2006-12-19 | 2008-06-26 | Dow Global Technologies, Inc. | Assemblages de panneaux encapsulés et leur procédé de fabrication |
| CN101245182B (zh) * | 2007-02-15 | 2010-09-01 | 北京高盟新材料股份有限公司 | 密封胶用耐高温耐水聚氨酯组合物及其制备方法 |
| US7819964B2 (en) * | 2007-02-16 | 2010-10-26 | Dow Global Technologies Inc. | System for bonding glass into a structure |
| BRPI0809711A2 (pt) * | 2007-04-24 | 2014-10-07 | Dow Global Technologies Inc | " método para ligar um primeiro substrato a um segundo substrato, conjunto de substratos, kit para o método para ligar um primeiro substrato a um segundo substrato, promotor de adesão para uma composição de primer, método pára melhorar o desempenho de uma composição de primer e composição de primer" |
| KR101139026B1 (ko) * | 2007-04-24 | 2012-04-26 | 다우 글로벌 테크놀로지스 엘엘씨 | 옥사졸라딘을 포함하는 1-성분 유리 하도제 |
| ATE544797T1 (de) * | 2007-04-24 | 2012-02-15 | Dow Global Technologies Llc | Zusatz für grundierungszusammensetzungen |
| CN101050223B (zh) | 2007-05-14 | 2010-12-01 | 张群朝 | 含硅烷或功能聚硅氧烷改性的异氰酸酯类三聚体及其制备方法 |
| KR101048979B1 (ko) * | 2007-05-30 | 2011-07-12 | 다우 글로벌 테크놀로지스 엘엘씨 | 유리 및 유리 상의 세라믹 에나멜을 접착제 접착을 위해 준비시키는 방법 |
| EP2011809A1 (fr) * | 2007-07-03 | 2009-01-07 | Sika Technology AG | Composition de polyuréthane comportant des amines tertiaires et de l'andhydidosilane |
| WO2009009159A1 (fr) * | 2007-07-12 | 2009-01-15 | Dow Global Technologies, Inc. | Compositions de primaire colorées, et procédés |
| BRPI0813070B1 (pt) * | 2007-07-23 | 2020-10-13 | Dow Global Technologies Inc | composição de duas partes e método para colar dois ou mais substratos juntos |
| BRPI0817385A2 (pt) * | 2007-11-07 | 2015-03-31 | Dow Global Technologies Inc | Composição e método para ligar vidro ou um plástico revestido com camada resistente à abrasão a um substrato |
| US8147974B2 (en) | 2007-12-18 | 2012-04-03 | Dow Global Technologies Llc | Protective coating for window glass having enhanced adhesion to glass bonding adhesives |
| US20100266855A1 (en) * | 2007-12-27 | 2010-10-21 | E. I. Du Pont De Nemours And Company | Adhesion-promoting agent for protective coatings |
| JP2009242516A (ja) * | 2008-03-31 | 2009-10-22 | Aica Kogyo Co Ltd | 硬化性樹脂組成物およびそれを用いた再はく離型粘着フィルム |
| WO2009146321A1 (fr) | 2008-05-30 | 2009-12-03 | 3M Innovative Properties Company | Substrats fonctionnalisés par ligand |
| EP2294118B1 (fr) | 2008-05-30 | 2012-07-04 | 3M Innovative Properties Company | Procédé de production de substrats fonctionnalisés par des ligands |
| BRPI0912919B1 (pt) * | 2008-08-22 | 2019-04-24 | Dow Global Technologies Llc | Composição bicomponente e método para ligar dois ou mais substratos entre si |
| JP5312602B2 (ja) * | 2008-10-29 | 2013-10-09 | ダウ グローバル テクノロジーズ エルエルシー | 長いオープンタイムを有するプライマーを含有する低エネルギー表面接着システム |
| EP2382254B1 (fr) * | 2008-12-23 | 2017-08-16 | Dow Global Technologies LLC | Adhésif utile pour installer des fenêtres de véhicule permettant une sortie de chaîne rapide |
| WO2010151447A1 (fr) | 2009-06-23 | 2010-12-29 | 3M Innovative Properties Company | Article non tissé fonctionnalisé |
| US8377672B2 (en) * | 2010-02-18 | 2013-02-19 | 3M Innovative Properties Company | Ligand functionalized polymers |
| KR101786140B1 (ko) | 2010-03-03 | 2017-10-17 | 쓰리엠 이노베이티브 프로퍼티즈 컴파니 | 리간드 구아니디닐 기능화된 중합체 |
| EP2545010B1 (fr) | 2010-03-08 | 2015-01-21 | Dow Global Technologies LLC | Composition d'apprêt à base d'eau pour adhésifs à fonctions isocyanate et silane |
| US9200160B2 (en) * | 2010-03-29 | 2015-12-01 | Momentive Performance Materials Inc. | Silylated polyurethane/polyorganosiloxane blend and sealant composition and fumed silica composition containing same |
| CN103270092B (zh) | 2010-11-01 | 2014-10-01 | 陶氏巴西股份有限公司 | 具有一个或多个改性表面以改善其与多异氰酸酯官能粘合剂粘附的聚烯烃 |
| DK2638090T3 (da) * | 2010-11-11 | 2015-05-04 | Dow Global Technologies Llc | Polyurethanbaseret tætningsmiddel til isoleret glas |
| BR112013015539A2 (pt) | 2010-12-20 | 2016-09-20 | Dow Global Technologies Llc | composição e método para ligar dois ou mais substratos entre si |
| CN103370350B (zh) | 2011-02-17 | 2015-05-27 | 陶氏环球技术有限责任公司 | 含有碳酸钙的含烷氧基硅烷的聚氨酯粘合剂组合物 |
| WO2012151085A1 (fr) | 2011-05-03 | 2012-11-08 | Dow Global Technologies Llc | Composition à durcissement accéléré contenant un prépolymère à fonctionnalité isocyanate |
| WO2012151086A1 (fr) | 2011-05-03 | 2012-11-08 | Dow Global Technologies Llc | Adhésif double durcissage utile pour le collage au verre |
| WO2013070227A1 (fr) | 2011-11-10 | 2013-05-16 | Momentive Performance Materials Inc. | Composition durcissable à l'humidité contenant un polymère possédant des groupes silyles |
| EP2776162B1 (fr) | 2011-11-10 | 2017-01-04 | Momentive Performance Materials Inc. | Composition d'organopolysiloxane durcissable à l'humidité |
| EP2791265A4 (fr) | 2011-12-15 | 2016-01-13 | Momentive Performance Mat Inc | Compositions de polyorganosiloxane durcissables à l'humidité |
| WO2013090127A1 (fr) | 2011-12-15 | 2013-06-20 | Momentive Performance Materials, Inc. | Compositions d'organopolysiloxane durcissables par l'humidité |
| KR20140116885A (ko) | 2011-12-29 | 2014-10-06 | 모멘티브 퍼포먼스 머티리얼즈 인크. | 수분 경화성 오가노폴리실록산 조성물 |
| EP2617690B1 (fr) * | 2012-01-19 | 2017-11-22 | Corning Incorporated | Procédé de décoration de verre chimiquement renforcé |
| US9493604B2 (en) | 2012-02-21 | 2016-11-15 | Dow Global Technologies Llc | Compositions containing aromatic isocyanate functional components and aliphatic aromatics isocyanate functional components having improved cure speed |
| US9499727B2 (en) | 2012-07-16 | 2016-11-22 | Dow Global Technologies Llc | Curable compositions containing isocyanate functional components having improved durability |
| WO2014051569A1 (fr) | 2012-09-26 | 2014-04-03 | Dow Global Technologies Llc | Produit d'étanchéité à base de polyuréthane pour du verre, isolé |
| EP2904039B1 (fr) | 2012-10-08 | 2020-10-07 | Dow Global Technologies LLC | Collage accéléré d'un adhésif à fonction isocyanate sur des plastiques renforcés par des fibres |
| US9416301B2 (en) | 2012-11-08 | 2016-08-16 | Dow Global Technologies Llc | Ultrafast dual cure adhesive useful for bonding to glass |
| CN104870506B (zh) | 2012-12-21 | 2017-11-14 | 陶氏环球技术有限责任公司 | 适用于安装车辆窗户的粘合剂 |
| EP2935384B1 (fr) | 2012-12-21 | 2020-09-02 | Dow Global Technologies LLC | Adhésif à durcissement rapide utile pour un collage au verre |
| EP3378905A1 (fr) | 2013-02-15 | 2018-09-26 | Momentive Performance Materials Inc. | Système antisalissure comprenant un hydrogel de silicone |
| TW201434882A (zh) | 2013-03-13 | 2014-09-16 | Momentive Performance Mat Inc | 可濕氣固化之有機聚矽氧烷組成物 |
| EP2994501A2 (fr) | 2013-05-10 | 2016-03-16 | Momentive Performance Materials Inc. | Compositions d'organopolysiloxane durcissables par l'humidité à température ambiante catalysées par un non-métal |
| US9663621B2 (en) | 2013-08-23 | 2017-05-30 | Momentive Performance Materials Inc. | Moisture curable compositions |
| CN105793326B (zh) | 2013-11-26 | 2020-07-21 | 莫门蒂夫性能材料股份有限公司 | 具有金属-芳烃配合物的可湿固化的组合物 |
| CN106257984B (zh) | 2014-05-08 | 2019-08-30 | 陶氏环球技术有限责任公司 | 可用于粘结玻璃的可湿致固化聚氨酯粘合剂组合物的加速固化 |
| WO2016137881A1 (fr) | 2015-02-23 | 2016-09-01 | King Industries | Compositions de revêtement durcissables à base de polymères fonctionnalisés au silane |
| US20210207011A1 (en) | 2016-02-17 | 2021-07-08 | Dow Global Technologies Llc | Compositions containing isocyanate functional prepolymers and quaternary ammonum modified nanoclays |
| EP3445829B1 (fr) | 2016-04-19 | 2022-05-18 | Dow Global Technologies LLC | Composition aqueuse de substratage à long temps ouvert pour adhésifs fonctionnels d'isocyanate et silane |
| KR102458390B1 (ko) * | 2016-11-14 | 2022-10-24 | 세키스이가가쿠 고교가부시키가이샤 | 습기 경화형 수지 조성물 및 조립 부품 |
| EP3645641B1 (fr) | 2017-06-26 | 2021-08-11 | Dow Silicones Corporation | Copolymère silicone-polyéther, produits de scellement le comprenant, et procédés associés |
| WO2019068083A1 (fr) | 2017-09-29 | 2019-04-04 | Dow Global Technologies Llc | Adhésif à fonction isocyanate se liant sans couche d'apprêt à un revêtement à base de polyol acrylique silané |
| KR102052164B1 (ko) * | 2018-01-30 | 2019-12-04 | 주식회사 케이씨씨 | 폴리우레탄 수지 조성물 |
| KR102021588B1 (ko) * | 2018-01-30 | 2019-09-16 | 주식회사 케이씨씨 | 폴리우레탄 수지 조성물 |
| US20210071053A1 (en) | 2018-02-02 | 2021-03-11 | DDP Specialty Electronic Materials US, Inc. | Adhesive useful for installing vehicle windows |
| KR102612630B1 (ko) | 2018-02-02 | 2023-12-14 | 디디피 스페셜티 일렉트로닉 머티리얼즈 유에스, 엘엘씨 | 차량 윈도우 설치에 유용한 접착제 |
| KR102659220B1 (ko) * | 2018-04-30 | 2024-04-23 | 다우 글로벌 테크놀로지스 엘엘씨 | 이소시아네이트-말단 실란계 2액형 접착제 조성물 및 이의 제조 방법 |
| WO2020022408A1 (fr) * | 2018-07-25 | 2020-01-30 | 東ソー株式会社 | Composition de polyisocyanate contenant un groupe allophanate, composition de formation de résine de polyuréthane, matériau d'étanchéité, module de membrane |
| WO2020116283A1 (fr) * | 2018-12-05 | 2020-06-11 | サンスター技研株式会社 | Adhésif à base d'uréthane pour automobile |
| KR102051295B1 (ko) * | 2018-12-07 | 2019-12-04 | 주식회사 케이씨씨 | 폴리우레탄 수지 조성물 |
| EP3898780A2 (fr) | 2018-12-21 | 2021-10-27 | Dow Silicones Corporation | Copolymère silicone-organique, produits de scellement le comprenant, et procédés associés |
| US12146034B2 (en) | 2018-12-21 | 2024-11-19 | Dow Silicones Corporation | Silicone-polyester copolymer, sealants comprising same, and related methods |
| EP3898782B1 (fr) | 2018-12-21 | 2025-06-25 | Dow Silicones Corporation | Copolymère silicone-polyacrylate, produits de scellement comprenant ce dernier, et procédés associés |
| US11760841B2 (en) | 2018-12-21 | 2023-09-19 | Dow Silicones Corporation | Silicone-polycarbonate copolymer, sealants comprising same, and related methods |
| WO2020263663A1 (fr) | 2019-06-25 | 2020-12-30 | Ddp Specialty Electronic Materials Us, Llc | Composition adhésive de polyuréthane à durcissement accéléré |
| EP4100452B1 (fr) * | 2020-02-03 | 2024-12-25 | DDP Specialty Electronic Materials US, LLC | Matériau d'interface thermique à base de polyuréthane comprenant des prépolymères d'uréthane à terminaison silane |
| CN117280004A (zh) | 2021-03-09 | 2023-12-22 | 迈图高新材料公司 | 基于硅的组合物及其应用 |
| WO2023215360A1 (fr) | 2022-05-04 | 2023-11-09 | Dow Silicones Corporation | Copolymère de silicone-polyéther, agents d'étanchéité le comprenant, et procédés associés |
| WO2023229913A1 (fr) | 2022-05-23 | 2023-11-30 | Momentive Performance Materials Inc. | Composition de revêtement protecteur pour métaux et surfaces polymères |
| CN119039929B (zh) * | 2024-10-28 | 2025-03-07 | 山东凯恩新材料科技有限公司 | 一种耐水的芯片灌封胶及其制备方法 |
Family Cites Families (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3372083A (en) * | 1964-03-11 | 1968-03-05 | Master Mechanics Company | Compositions and articles from the reaction of an isocyanate terminated polyurethaneand the isocyanate adduct of bitumen |
| NL128384C (fr) * | 1965-07-15 | 1900-01-01 | ||
| US3627722A (en) * | 1970-05-28 | 1971-12-14 | Minnesota Mining & Mfg | Polyurethane sealant containing trialkyloxysilane end groups |
| CA1015488A (en) * | 1972-02-17 | 1977-08-09 | Seiji Nagahisa | Polyurethane composition |
| US4284751A (en) * | 1980-05-14 | 1981-08-18 | Products Research & Chemical Corp. | Polyurethane sealant system |
| US4345053A (en) * | 1981-07-17 | 1982-08-17 | Essex Chemical Corp. | Silicon-terminated polyurethane polymer |
| US4374237A (en) * | 1981-12-21 | 1983-02-15 | Union Carbide Corporation | Silane-containing isocyanate-terminated polyurethane polymers |
| JPS6055022A (ja) * | 1983-09-07 | 1985-03-29 | Sunstar Giken Kk | ポリウレタン樹脂組成物 |
| DE3410582A1 (de) * | 1984-03-22 | 1985-09-26 | Wacker-Chemie GmbH, 8000 München | Sic-gebundene biuretgruppen enthaltende siliciumverbindungen, verfahren zu ihrer herstellung und verwendung solcher organosiliciumverbindungen |
| US4539345A (en) * | 1985-02-04 | 1985-09-03 | Minnesota Mining And Manufacturing Company | Moisture-curable polyurethane composition |
| US4687533A (en) * | 1985-08-26 | 1987-08-18 | Essex Specialty Products, Inc. | Bonding method employing moisture curable polyurethane polymers |
| US4625012A (en) * | 1985-08-26 | 1986-11-25 | Essex Specialty Products, Inc. | Moisture curable polyurethane polymers |
| US4720536A (en) * | 1986-06-06 | 1988-01-19 | Uop Inc. | Blends of secondary alkyl aromatic diamines and polyhydric alcohols as curing agents in polyurethane manufacture |
| US4758648A (en) * | 1986-10-20 | 1988-07-19 | Essex Specialty Products, Inc. | High speed cure sealant |
| KR950006938B1 (ko) * | 1986-11-19 | 1995-06-26 | 시바-가이기 아게 | 접착 촉진제 |
| JP2708063B2 (ja) * | 1988-11-28 | 1998-02-04 | サンスター技研株式会社 | ガラス用プライマー組成物 |
| GB8912172D0 (en) * | 1989-05-26 | 1989-07-12 | Bostik Ltd | Moisture-curing,one-part polyurethane compositions |
| IT1251489B (it) * | 1991-09-17 | 1995-05-15 | Enichem Sintesi | Policarbonati dioloterminati |
| US5342867A (en) * | 1992-10-06 | 1994-08-30 | Ciba-Geigy Corporation | Adhesion promoters |
-
1993
- 1993-09-09 BR BR9307293A patent/BR9307293A/pt not_active IP Right Cessation
- 1993-09-09 AU AU51031/93A patent/AU675083B2/en not_active Ceased
- 1993-09-09 JP JP50849794A patent/JP3466610B2/ja not_active Expired - Lifetime
- 1993-09-09 CA CA002144530A patent/CA2144530C/fr not_active Expired - Lifetime
- 1993-09-09 WO PCT/US1993/008485 patent/WO1994009046A1/fr not_active Ceased
- 1993-09-09 KR KR1019950701401A patent/KR100285097B1/ko not_active Expired - Lifetime
- 1993-10-12 TW TW082108433A patent/TW268045B/zh active
- 1993-10-12 ZA ZA937549A patent/ZA937549B/xx unknown
- 1993-10-12 CN CN93118939A patent/CN1054148C/zh not_active Expired - Lifetime
-
1996
- 1996-08-09 US US08/690,301 patent/US5623044A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| KR950703589A (ko) | 1995-09-20 |
| KR100285097B1 (ko) | 2001-03-15 |
| WO1994009046A1 (fr) | 1994-04-28 |
| CA2144530A1 (fr) | 1994-04-28 |
| CN1086242A (zh) | 1994-05-04 |
| US5623044A (en) | 1997-04-22 |
| ZA937549B (en) | 1995-04-12 |
| BR9307293A (pt) | 1999-06-01 |
| CN1054148C (zh) | 2000-07-05 |
| AU5103193A (en) | 1994-05-09 |
| TW268045B (fr) | 1996-01-11 |
| JP3466610B2 (ja) | 2003-11-17 |
| JPH11507399A (ja) | 1999-06-29 |
| AU675083B2 (en) | 1997-01-23 |
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